In this candid monologue, Bob London reflects on the societal script that many follow—good grades, a prestigious school, a corporate job, marriage, and home ownership—despite there being no predetermined itinerary. He uses the round‑peg‑in‑a‑square‑hole metaphor to describe his own early career, where he forced himself into corporate roles that didn’t suit his strengths, leading to stress, anxiety, and multiple firings. London explains that what is often labeled “imposter syndrome” can actually be a mismatch between a person’s abilities and their role. The turning point came when he discovered consulting, which allowed him to identify and leverage his true strengths, giving him freedom and fulfillment. He urges listeners to question the conventional career path, be honest about fit, seek trusted feedback about their strengths, and recognize that they have agency to make different choices, even when financial pressures seem to limit options. The overall message is supportive and encouraging: rather than blaming oneself for feeling like an impostor, assess whether the role is the right fit and actively pursue work that aligns with one’s genuine abilities.
Chapters
A few years ago when my— one of my kids especially, but both were in, I guess, high school, there was this whole discussion about round pegs and square holes, and they didn't really understand. I'm not sure I really understood, to be honest with you. But I said to them, when you're born, you know, no one hands you an itinerary and says you're going to go get good grades and go to a brand name school you know, big school and get married, have kids, buy a house, get a job in business, whatever that is. Yes, I'm holding a beer. And but no one hands you an itinerary. But why do we feel like that is the path? Because everyone else is doing it. And boy, I wish someone had told me that years ago. And I, I'm fortunate that I was able to have the experiences I had, painful as they were in some cases, so that I could share it with my kids because they might just be individuals and not cut out for the path that all their friends are on, for example. And so I freely admit to the— I don't know if I've ever said it on video, but I freely admit that I was a round peg trying— square peg trying to get into a round hole for most of the first half of my career. In the corporate world. It did not serve me well. You can see a lot of follicles lost from stress and stuff. I was not a good manager, not a good leader. I was a stressed-out person, very anxious, uh, still manage anxiety. But, um, it wasn't until I found consulting and could spread my wings and continually ask people, you know, what am I really good at, you know, and sort of just do the work that, that where that led me, which led me to where I am today. And so, um, sometimes imposter syndrome is not a syndrome. It's very real because you're in a role that you are not suited for. If you are looking for a job because you are unemployed, just be honest with yourself. Maybe it's time to check in. I got fired more than once. Each time there was a message being sent to me and I was not in tune with what that message was. And so I wish I had. No regrets though, it led me to a great place. So the point is, don't just get on the path. Question it. Question the path. It may not be imposter syndrome. Maybe you just aren't a fit. I'm not saying anything horrible. I'm saying we all should be making choices. We all have choices and freedom. Yes, it seems like we're locked in for financial reasons or whatever, but the reality is we all have choices of what we're doing every day. And yeah, I'm lucky I can say it. I'm a consultant. I can do whatever I want. Well, I didn't come to that choice by myself. And so I would encourage everyone, no matter where you are in your situation, it's not that you're an impostor, it's not that you don't have impostor syndrome, just question yourself, question yourself. Ask people that you know and trust, what am I great at? There's something I'm really good at. Maybe that's a skill that you can take with you and build on. Try it. Good message.